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Trail Running Calendar near Boston 2026-2027

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Explore the top trail runs near Boston for 2026-2027! We've gathered 15 exciting races in the area. Check out our detailed list below to find your next local race.

November 2026
Nov
7
Sa

TJHS Color Fun Run/Walk

Road Race Trail Run 2 mi 5 km
Nov
14
Sa

Last Trail Standing

Trail Run 5 km 8 mi 25 km 50 km
Nov
26
Th

Seneca Valley Cross Country Turkey Chase

Trail Run 5 km
December 2026
Dec
20
Su

Ugly Sweater 5K - Oakdale

Trail Run 5 km
January 2027
Jan
1
Fr

New Year's Resolution Run 5K - Oakdale

Trail Run 3 mi
Monthly updates for Boston

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March 2027
Mar
6
Sa

Northside Nemesis

Urban Trail 25 km 16 mi
April 2027
Apr
3
Sa

Soles for Songs

Trail Run 5 km 10 km 15 km
Apr
10
Sa

Farther Together Endurance Challenge

Trail Run Backyard Ultra 2 mi 5 mi
Apr
18
Su

Rise Up Hero Trail Runs at Settlers Cabin Park

Trail Run 5 km 8 mi 25 km 50 km
May 2027
May
29
Sa

Outlast Pittsburgh

Trail Run Backyard Ultra 5 km 18 mi
June 2027
Jun
6
Su

South Ridge Trail Challenge

Trail Run 4 mi 7 mi 12 mi 33 mi
July 2027
Jul
11
Su

Murrysville Monster Trail Races

Trail Run 6 mi 12 mi
August 2027
Aug
1
Su

Two Face 10K

Trail Run 6 mi 7 mi 13 mi
Aug
28
Sa

Baker Trail Ultrachallenge

Trail Run 50 mi
October 2027
Oct
23
Sa

North Ridge Nightmare

Trail Run 7 km 13 km
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